Usually when Jennie would plan something for a friend's birthday it would involve restaurants and dancing. Not renting a hotel room for just the two of them. Jennie always loved hearing about Riley's unique line of work. It was like Riley was made for this job. Already she could look down on most men, being six foot tall then sporting her stiletto boots she'd tower over her clients. Ironic how many of them were alpha-male executives. The type that could make their underlings quiver when they entered the room. Yet Riley would have them literally licking the bottom of her shoes. And they would thank her for it. But Jennie was uniquely qualified for Riley's dream client. Feminizing a boyish woman.
Normally forced feminization involved making the men dress in skimpy women's clothes. Makeup, wigs, all of it. Make them experience all the stuff normally only women had to go through. Some would even be sent on a task out in public. Jennie felt like a hypocrite laughing at them. Most of her wardrobe consisted of loosely fitting hoodies and baggy pants. Unlike Riley she didn't have a head turning bosom. A butt that could rip a dress. A body that was toned and sculpted. Maybe that contributed to why she so readily agreed to Riley's birthday wish.
The bathroom door cracked open. Jennie leaned forward. Excited to see her friend in her work uniform. Riley came out. Clad in leather. A bra that pushed together her heavy breasts and gave her enough cleavage to smother a full grown man. Straps criss crossing over her midriff. All connected to a metal ring around her belly button. Like a corset but showing more skin. The bottoms were a high waisted thong. Exposing her hips. The back of it was swallowed by her thick booty. High heeled boots that went just below her knee. With them on she was over a foot taller than Jennie.
"Holy shit Riley, you look hot," Jennie stood up and looked over at her friend. A nervous giggle.
But Riley scowed and cracked her riding crop. Her long stride took her quickly to her friend. Grabbing her by the throat. Applying enough pressure to show she was in control. "Don't speak to me so casually. You may call me mistress and only mistress. Understand?"
Jennie was shocked. Aroused but shocked. Being handled so forcefully by the woman she routinely grabbed a friendly cup of coffee and felt so subversive. "Sorry Mistress. I was only trying to compliment you," Jennie spoke softly. Feeling herself falling into character.
"A compliment from you? Meaningless. With how you're dressed I can't even tell if you're a man or woman," Riley stepped back. A disappointed look down her nose at Jennie. Who was slouched. Fist and arms pressed firmly into her sides
"I'm a..." another crack of Riley's riding crop made Jennie interrupt herself with a gasp.
"Silence. I'll just find out for myself," Riley's voice shook the room. She clawed the side of Jennie's pants and yanked them to the floor. Taking her panties with them. Even through her pressed-together thighs and thick, dark bush she could still feel the cold hotel air hit her wet cooch. "My god. Do you not take any effort with your appearance? I still can't tell through all that hair. Spread them," Riley ordered by tapping the inside of Jennie's knees with her riding crop.
Jennie was unable to even think about defying her orders. She obediently adjusted her stance. Feet more than shoulder width apart. As soon as she did Riley's large, yet soft hand reached down and pressed between her legs. Jennie gasped, "Riley!" But before she could say more Riley's other hand slapped across her face. Just enough to give her a soft sting.
"I'm not going to warn you again. You may only call me Mistress," her open hand began rubbing between Jennie's thighs. "Strange. I don't feel a cock. I don't feel any balls. I only feel a pussy. Do you have a pussy?"
"Yes Mistress. I have a pussy," Jennie dared not cross her again.
"On your knees," Riley ordered and Jennie dropped as fast as gravity let her. Feeling so small she feared Riley could crush her with one misstep. Riley stepped around her, Jennie could sense her dominant presence looking down at the back of her head. Riley jerked her hoodie over her body. Jennie had to brace herself to not be knocked over. Her t-shirt and bra quickly followed. Jennie was stripped nude. On her knees looking up at her towering, leather-clad friend.
"So you have tits too huh? You are a lady," Riley did a slow trot around Jennie. That look of disappointment plastered on her face. "Why don't you dress like it?" Jennie hesitated and looked down at the ground. Unsure how to answer. Another crack of Riley's crop made her head shoot up. Riley had a wide stance right in front of her.
